The Unique Work of a Product Executive at a Mid-Size Company

In between “scrappy startup” and “enterprise behemoth” lies the mid-size company. With hundreds—or maybe even one or two thousand employees—organizations in this size range don’t often grab many headlines. For product executives, their firm’s growth from a small startup to mid-size going concern means a few key changes in how they build and lead their teams.

They may not have the appeal of a potential rocketship or the brand-name recognition of a unicorn. But mid-size companies make up a massive chunk of the corporate landscape, employing around one-quarter of all U.S. workers. Simultaneously, some of these companies may be “passing through,” the mid-size state on their way to enjoy a lengthy existence in this realm.

Failing to recognize that things are much different when total headcount hits the thousands can prove costly. What worked when everyone knew your name doesn’t always fly when you’re becoming just another face in a growing crowd

Successfully navigating this shift requires some key actions from product executives. It also requires significant alterations in your mindset.

5 Ways That Work Changes for Product Executives at Mid-Size Companies

1. Prioritization becomes more important.

When an organization grows, it would be natural to assume that you can deploy more resources to take on a broader set of initiatives. After all, product executives are suddenly blessed with larger teams of engineers waiting for marching orders.

But thinking that the rules of prioritization no longer apply can be a fatal move. Remember, even though there are more employees and bigger budgets, things are still precarious.

Mid-size firms operate in a continual state of purgatory. They must still be thrifty and selective. They don’t have nearly the same resources as their larger, enterprise-class competitors who can outspend you. Even if your product is functionally superior, larger companies can fund more loss-leading land grabs and concierge-level customer service.

Meanwhile, your growing company will inevitably lose some of its nimbleness. You won’t be able to turn on a dime or take as risky bets like you did when you were a smaller startup.

To survive this trepidacious time period in your company’s growth, you must be extra sure that each move is the right one. That means it’s no time to abandon your ruthless adherence to prioritization practices. Nor can you quit using one or more of the available frameworks to identify the most opportune investments.

2. Saying “no” more often and to more people.

Your role as gatekeeper also won’t get any easier just because you’re at a bigger company.

The increased resources available may be accompanied by stakeholders believing that now available for more requests.

The overall output of the company should increase. But there must still be a rigorous vetting and scheduling process for each request. After all, what increases the degree of difficulty for product executives is the increase in requests.

As your customer base grows, your ability to kowtow to any particular client’s demands shrinks.

Early adopters used to getting their way most of the time might not like hearing “no” on a more regular basis. Explaining why their pet project can’t cut requires tact and positioning.

Be sure everyone understands that part of maturing into a larger company means you can’t make everyone happy all of the time. Another approach is attaching a price tag to custom work that might have previously been handled gratis. There are costs of delay to consider. Charging customers to get their specific requests implemented might quiet or slow down their demands.

Saying no will also become more common internally. Not only must longtime coworkers get used to the new, more tightly controlled approach. But, there will be a whole newimpac slate of stakeholders that don’t possess the same institutional knowledge.

Stand firm and hold every request to the same level of scrutiny. With increasing volumes, it’s more important than ever to stick with consistent processes. Shut down attempts to circumvent them.

Closing the loop and increasing communication about decisions and status is also essential. Not everyone will be privy to the same information or as familiar with how and when decisions are made.

3. Different socializing strategy.

With more colleagues to connect with and the same amount of time to do so, product executives at mid-sized companies must adopt a different approach to getting everyone aligned, informed, and excited about the product’s plans.

Individual sessions with key stakeholders remain vital. But not everyone can darken your door for their personal tour.

Leveraging all-hands meetings is one tactic for getting this done. Securing a slot on the agenda and presenting the overarching strategy and rationale for key product decisions is a highly efficient way to convey this information and build consensus.

Another tool product executives can use is a cloud-based product roadmapping solution (like ProductPlan). Using this software, product management can ensure that everyone sees the latest version of the product roadmap. They can also create custom views for different teams or management layers that offer varying levels of detail.

Utilizing this, every coworker will have access to the strategic plan on-demand. This saves the product team from spending all their time on a continual cycle of meetings and review sessions. With the could roadmap, you offer coworkers the opportunity to subscribe and receive updates for changes. Thus, everyone will have a better chance to remain aware of the current status and any significant strategic or scheduling shifts.

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4. A need for greater alignment with key goals and objectives.

With a larger and more diverse workforce, there will inevitably be disparate levels of understanding of why a given project or feature is strategically important and worthy of a slot in the development queue. That’s why it’s imperative to position things in terms of the “why” rather than the “what.”

It doesn’t really matter that you’re building an import function before working on a group collaboration feature. It’s even less relevant that you’ve slotted a particular social media integration on the back burner indefinitely. What’s far more consequential is the business objective you’re trying to achieve.

Using themes on your product roadmaps elevated the conversation to how the product strategy will improve KPI. This roadmap aligns with the goals prioritized by the management team. It broadcasts what’s important to the product roadmap. It has a direct relationship to the overarching corporate strategy.

Using a colorful, visual product roadmap, you and your team can stop bickering with individuals about why their favorite shiny object isn’t being worked on. Instead, it frames the entire exchange in terms of broad strategic strokes. The roadmap provides an unimpeachable justification for prioritizing specific items—all chosen based on how they roll up under these themes and impact KPIs.

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5. Keeping track of the details.

The bigger the organization, the more there is to track. Products are likely becoming more complex as new product lines emerge. There are so many more people checking in code, making requests, interacting with customers, and telling the product’s story to the market. There’s simply no way a single person can stay on top of it all.

Here is where delegation becomes an indispensable skill for a product executive. Instead of trying to do a little bit of everything, it’s time to fully deputize the more junior members of your team and grant them additional ownership of their areas.

This requires clear lines of communication and true empowerment. You must trust them to make wise, data-driven decisions and escalate when needed. It also requires collaborative product planning tools to create a consistent platform for the work and message to the rest of the organization.

As you learn to let some details go and relegate your iron grip on all things product, you can take some key precautions to ensure your team doesn’t drop the ball. For example, as product implementation teams grow and the breadth of enhancements and changes increases, they should be careful to ensure the technical debt isn’t piling up behind the scenes. You don’t want to wait for the most inopportune moment for technical debt to rear its ugly head.

Stakeholder alignment is also a constant area of concern. You don’t want your relatively independent minions to cause problems by not ensuring cross-functional buy-in and communication. Creating consistent processes and templates for key steps in the product development cycle can help corral individual contributors and instill a reliable format to how decisions are made and disseminated.


Unique Opportunities for Product Executives at Mid-sized Companies

Mid-size companies can be an assortment of DIY tactics and well-defined processes. They straddle the just-get-it-done mentality of a smaller firm and the large-scale organization of enterprises. Creating enough scaffolding in the product management discipline without choking off flexibility and creativity can be a tricky needle to thread.

But leading product initiatives in these settings can be incredibly rewarding. These companies are still small enough to be a prominent leader. But they are flexible enough to change courses and seize opportunities when they arise. With more cash in the bank and more people to throw at problems, they can also often get more done with higher quality and speed than a startup’s skeleton crew can achieve.

It’s an opportunity for newer product leaders to stretch themselves, build a larger team, and create scalable processes to help them for the rest of their careers. For veterans, it’s a chance to make a bigger impact on the company’s overall strategic direction and success while dealing with less politics and red tape.
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Make the most of your time as a product executive at a mid-size firm by leaning on product ops to identify best practices and tools designed for transparency, scalability, and streamlined decision making.